3-[(1′-hydroxy-1′-phenyl)methyl]-tetrahydropyran-4-one | 944109-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 3-[(1′-hydroxy-1′-phenyl)methyl]-tetrahydropyran-4-one
• 英文别名: (2S,1'R)-3-(hydroxyphenylmethyl)tetrahydropyran-4-one；3-[(1'-hydroxy-1'-phenyl)-methyl]-tetrahydropyran-4-one；tetrahydro-3-(hydroxyphenylmethyl)-4H-pyran-4-one；(S)-3-((R)-hydroxy(phenyl)methyl)-tetrahydropyran-4-one；(3S)-3-[(R)-hydroxy(phenyl)methyl]oxan-4-one
• CAS: 944109-63-1
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: ZDFZHZYWGCRUEP-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四氢吡喃酮 、 苯甲醛 在 (4R)-N-((S)-1-hydroxy-4-methyl-1,1-diphenylpentan-2-yl)thiazolidine-4-carboxamide 、 水 、 sodium chloride 作用下， 以75%的产率得到3-[(1′-hydroxy-1′-phenyl)methyl]-tetrahydropyran-4-one
  参考文献：
  名称：

  用于有机和水性介质中对映选择性直接羟醛反应的高效小型有机分子

  摘要：

  已经从天然可用的氨基酸衍生出了一系列高效的有机催化剂，用于在有机和水性介质中进行对映选择性的直接羟醛反应。使用1 mol％的催化剂，可以在更大范围的底物上以高非对映选择性（最高99：1）和对映选择性（最高> 99％ee）获得醛醇产物。结果表明，有机催化剂的结构特征对于在水性介质中获得高光学纯度的醛醇加合物具有至关重要的作用。此外，已经说明了水在增加反应速率和对映选择性中的作用。而且，醛醇缩合产物已被用于手性氨基醇的合成中，手性氨基醇用作建立复杂的天然产物的有用的中间体。

  DOI：

  10.1021/jo900548f

文献信息

• 3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
  作者：Sergio Rossi、Tiziana Benincori、Laura Maria Raimondi、Maurizio Benaglia

  DOI：10.1055/s-0039-1690777

  日期：2020.4

  This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride)

  该帐户总结了新的双杂芳族手性双膦氧化物的开发。3,3'-联噻吩基氧化膦 (BITIOPO) 已成功用作有机催化剂，以促进路易斯碱催化、路易斯酸介导的立体选择性转化。这些高度富电子的化合物与三氯甲硅烷基衍生物（烯丙基三氯硅烷和四氯化硅）结合，生成高价硅物质，在高度非对映选择性和对映选择性有机反应中充当手性路易斯酸。详细讨论了与这些应用程序相关的几个相关示例。
• SULFONAMIDE-BASED ORGANOCATALYSTS AND METHOD FOR THEIR USE
  申请人：Carter Rich Garrett

  公开号：US20100184986A1

  公开（公告）日：2010-07-22

  Organocatalysts, particularly proline sulfonamide organocatalysts, having a first general formula as follows are disclosed. Embodiments of a method for using these organocatalysts also are disclosed. The method comprises providing a disclosed organocatalyst, and performing a reaction, often an enantioselective or diastereoselective reaction, using the organocatalyst. Solely by way of example, disclosed catalysts can be used to perform aldol reactions, conjugate additions, Michael additions, Robinson annulations, Mannich reactions, α-aminooxylations, α-hydroxyaminations, α-aminations and alkylation reactions. Certain of such reactions are intramolecular cyclizations used to form cyclic compounds, such as 5- or 6-membered rings, having one or more chiral centers. Disclosed organocatalysts generally are much more soluble in typical solvents used for organic synthesis than are known compounds. Moreover, the reaction yield is generally quite good with disclosed compounds, as is their enantioselective and diastereoselective effectiveness.

  披露了具有如下一般公式之一的有机催化剂，尤其是脯氨酸磺酰胺有机催化剂。还披露了使用这些有机催化剂的方法的实施例。该方法包括提供一种披露的有机催化剂，并使用该有机催化剂进行反应，通常是立体选择性的反应或对映选择性反应。仅作为示例，披露的催化剂可用于进行aldol反应、共轭加成、Michael加成、Robinson环化反应、Mannich反应、α-氨基氧化、α-羟基胺化、α-胺化和烷基化反应。其中一些反应是分子内环化反应，用于形成具有一个或多个手性中心的环状化合物，例如5或6元环。披露的有机催化剂通常比已知的化合物更容易溶于用于有机合成的典型溶剂中。此外，使用披露化合物的反应收率通常相当好，它们的对映选择性和非对映选择性效果也很好。
• The application of a structurally simple, recyclable, and large-scale l-prolinamide catalyst for asymmetric aldol reactions
  作者：Zhi Guan、Yuan Luo、Bao-Qiang Zhang、Krystal Heinen、Da-Cheng Yang、Yan-Hong He

  DOI：10.1016/j.tetasy.2014.04.009

  日期：2014.5

  With heterocyclic ketones or cyclohexanone, the aldol reactions gave products in high yields and with respectable enantioselectivities (87–99% ee) and diastereoselectivities (up to >99:1 anti/syn). The catalyst could be recycled and reused up to seven times resulting in good yields and with good selectivities. This catalyst is also efficient in large-scale reactions with the enantioselectivities remaining

  一个高效，双功能催化剂脯氨酰胺，其由手性脯氨酸和的反式-cyclohexanediamine部分，准备和各种酮类和醛类的直接不对称羟醛缩合反应进行评价。该催化剂对含氧，硫或氮的杂环酮显示出令人印象深刻的催化活性，但尚未充分探索。基板范围还覆盖环状和无环酮。与杂环酮或环己酮，醛醇缩合反应，得到的产品在高收率和对映选择性尊敬（87-99％ee）和非对映选择性（高达> 99：1反/顺）。该催化剂可再循环和再利用起来，导致良好的收益率七次，具有良好的选择性。该催化剂也与保持在相同的水平在实验规模的反应对映选择性的大规模反应高效。
• Novel enantioselective direct aldol-type reaction promoted by a chiral phosphine oxide as an organocatalyst
  作者：Shunsuke Kotani、Yasushi Shimoda、Masaharu Sugiura、Makoto Nakajima

  DOI：10.1016/j.tetlet.2009.05.065

  日期：2009.8

  Chiral phosphine oxide successfully catalyzed the direct aldol-type reactions of cyclohexanone derivatives and benzaldehyde derivatives in high stereoselectivities. The reaction mechanism involves the in situ formation of trichlorosilyl enol ethers. The present reaction could be extended to the cross-aldol reactions between two aldehydes.

  手性氧化膦以高的立体选择性成功催化了环己酮衍生物和苯甲醛衍生物的直接羟醛型反应。反应机理涉及三氯甲硅烷基烯醇醚的原位形成。本反应可以扩展到两个醛之间的交叉-羟醛反应。
• <i>N</i>-(<i>p</i>-Dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: A Practical Proline Mimetic for Facilitating Enantioselective Aldol Reactions
  作者：Hua Yang、Rich G. Carter

  DOI：10.1021/ol801941j

  日期：2008.10.16

  A highly practical and readily available proline surrogate has been developed with improved solubility properties in common, nonpolar organic solvents. This sulfonamide-based catalyst has proven highly effective at facilitating enantioselective and diastereoselective aldol reactions with a range of substrates in nonpolar organic solvents in the presence of a single equivalent of water. Additionally

  一种高度实用且易于获得的脯氨酸替代品已被开发出来，其在常见非极性有机溶剂中的溶解度得到改善。事实证明，这种磺酰胺基催化剂在单当量水存在下，在非极性有机溶剂中能够非常有效地促进与一系列底物的对映选择性和非对映选择性羟醛反应。此外，在不存在任何有机溶剂的情况下，可以使用低至 2 mol% 的催化剂负载，并具有持续的高水平选择性。